The first main event for the Undertaker involved a clash with current WWF champion Psycho Sid. Wrestlemania 13 is mostly remembered for Steve Austin and Bret Hart's epic "I Quit" match, but the Undertaker was the one who closed the show with a big tombstone and title victory over Sid. By Wrestlemania main event standards the match was not very good, but the Undertaker was still able to get a solid performance out of a limited wrestler in Sid.

After Kane was introduced to the WWF the previous October, the Undertaker and his brother began their never-ending feud with their first Wrestlemania match. Kane was riding a huge wave of momentum as a monster heel, but the Undertaker still came out on top when he hit Kane with an impressive trifecta of tombstones in what was his best Wrestlemania match to date.

#8 Undertaker vs The Big Boss Man Wrestlemania XV

The first Hell in a Cell match to take place at Wrestlemania, the Undertaker disposed of the Big Boss Man rather quickly in under ten minutes. The match is probably best remembered for the post-match hanging of the Big Boss Man by the Brood from the top of the cell. Although the Undertaker was a major player in the WWF title and main event picture during the Attitude Era, his Wrestlemania matches were rather disappointing.

The first of the truly great Wrestlemania matches for the Undertaker came ten years after his first victory on the grandest stage of them all against a white-hot HHH. This was the first Undertaker match to feature the American Bad-Ass character and he took care of business in an exciting match that featured the two future legends brawling all over the Astrodome.

Ric Flair is the epitome of the big-time performer in wrestling. Whenever the lights get a little bit brighter Flair always steps it up a notch. Flair vs The Undertaker should have been an instant classic, and although the match was good-to-exceptional, it left the crowd feeling that something bigger could have taken place. This was the first match were the Undertaker acknowledged the streak, as he flashed ten fingers after he pinned the Nature Boy.

After two good/great Wrestlemania matches, the Phenom slipped back into his rut of working with limited wrestlers and trying his best to get a passable match out of them. Undertaker pinning men as large as A-Train and Big Show was certainly impressive, but seriously, how great can a match be if it involves Nathan Jones coming out to make the save?

#12 Undertaker vs Kane Wrestlemania XX

Kane had helped Mr. McMahon defeat the Undertaker in a buried alive match in November of 2003, and had since been claiming that the Undertaker was no more. However, mysterious signs of the Undertaker's return had begun to prop up on the road to Wrestlemania, leading to the brothers second match at Wrestlemania. The Undertaker returned in full Deadman get-up and pinned Kane to extend his streak to a dozen straight. Although the match was slightly disappointing, it was really all about the return to darkness for the Phenom.